Bodipy Dyes with Tunable Redox Potentials and Functional Groups for Further Tethering: Preparation, Electrochemical, and Spectroscopic Characterization
Bibliographic record
Abstract
The preparation, spectroscopic, and electrochemical characterization of a family of 16 new bodipy dyes with tunable redox potentials and versatile functional groups is reported. Electron-withdrawing or -donating groups (Et, H, Cl, or CN) at positions C2 and C6 enabled tuning the redox potentials within a ca. 0.7 eV window without significantly affecting either the HOMO-LUMO gap or the absorption and emission spectra. Hydroxymethyl or formyl groups at the meso (C8) position in turn provided a handle for covalent tethering to receptors and biomolecules of interest, which dispenses with the more commonly used meso-aryl moiety as a means to tag molecules. The dyes can thus be coupled to both electrophiles and nucleophiles. Importantly, it is shown that meso-formyl bodipy dyes are nonemissive and have significantly lower molar extinction coefficients compared to their meso-hydroxymethyl and meso-acetoxymethyl counterparts (which in turn are bright, with emission quantum yields in the range of 0.7-1). The nonemissive meso-formyl bodipy dyes thus provide unique opportunities as fluorogenic probes of nucleophilic attack and as fluorescent labeling agents where uncoupled fluorophores will not contribute to the fluorescence background. Overall, the new bodipy dyes reported here are promising candidates for the preparation of fluorescent sensors relying on photoinduced electron transfer and may find use in a number of fluorescent-labeling protocols.
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How this classification was reachedexpand
Full frame machine prediction
Teacher imitationNot calibrated prevalence, not ground truth. Human validation pending. The Gemma side is a direct model label for every work in the frame, read from the title-only record. The Codex side is a classifier learned from the 10,348 direct Codex labels and calibrated to design-weighted sample rates; fields without enough sample support carry no Codex call. Candidate is the union of the two sides; consensus is their intersection. These outputs are machine_predicted_unvalidated and are not human labels.
Distilled classifier scores by category (both heads)
| Category | Codex | Gemma |
|---|---|---|
| Metaresearch | 0.000 | 0.000 |
| Meta-epidemiology (narrow) | 0.001 | 0.000 |
| Meta-epidemiology (broad) | 0.000 | 0.000 |
| Bibliometrics | 0.000 | 0.000 |
| Science and technology studies | 0.000 | 0.000 |
| Scholarly communication | 0.000 | 0.001 |
| Open science | 0.000 | 0.000 |
| Research integrity | 0.001 | 0.001 |
| Insufficient payload (model declined to judge) | 0.001 | 0.000 |
Machine scores (provisional)
The two teacher heads of the student model, read on this work. A score orders the frame for review; it never asserts a category, and the validation status ships verbatim with every row.
Baseline scores from an immature model (maturity gate not passed, 7 training rounds). Scores rank; they never assert a category.
score_only:v0-immature-baseline · verbatim from the scoring run: score_only means the number may rank works, and no category label ships from itClassification
machine, unvalidatedMachine predicted; a candidate call from one source (direct Gemma or distilled Codex), not a consensus.
How this classification was reached, model by model and score by score, is at the end of the page under "How this classification was reached".